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Tunable Cu(I)-catalyzed site-selective dehydrogenative amination of β,γ-unsaturated hydrazones for divergent synthesis of pyrazol-4-ones and 1,6-dihydropyradazines

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Abstract

A new tunable Cu(I)-catalyzed site-selective dehydrogenative amination of β,γ-unsaturated hydrazones has been established using readily accessible dioxygen as a green oxidant. The presence of Cu2O/O2 regiospecifically accessed densely functionalized pyrazol-4-ones with one quaternary carbon-amino functionality, in which O2 acted as both a reaction component and an oxidant, whereas the employment of CuI/O2 as a catalytic oxidation system resulted in 1,6-dihydropyradazines with good yields.

Graphical abstract: Tunable Cu(i)-catalyzed site-selective dehydrogenative amination of β,γ-unsaturated hydrazones for divergent synthesis of pyrazol-4-ones and 1,6-dihydropyradazines

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Publication details

The article was received on 21 Aug 2017, accepted on 27 Sep 2017 and first published on 28 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00743D
Citation: Org. Chem. Front., 2018, Advance Article
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    Tunable Cu(I)-catalyzed site-selective dehydrogenative amination of β,γ-unsaturated hydrazones for divergent synthesis of pyrazol-4-ones and 1,6-dihydropyradazines

    D. Jiang, J. Hu, W. Hao, S. Wang, S. Tu and B. Jiang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00743D

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